The Obstacle Is The Way by Ryan Holiday: Book Summary, Key Lessons and Best Quotes

“The impediment to action advances action. What stands in the way becomes the way.” Marcus Aurelius

It’s this line from Marcus Aurelius, written nearly 2,000 years ago in his private diary, that served as the inspiration for the international bestseller The Obstacle Is The Wayby Ryan Holiday. It is a book that has become a cult classic and required reading for athletes, entrepreneurs, artists or anyone who is looking for a timeless framework for overcoming the obstacles and adversities life throws at us.

The book is inspired and rooted in the practical philosophy of Stoicism, but it does not explicitly make it about the philosophy. There is plenty written about Stoicism out there, much of it by some of the wisest and greatest thinkers who ever lived. The book does not rewrite what they have written—the originals are there for us to read. No philosophic writing is more accessible. It feels like it was written last year, not last millennium.

Some of these men and women faced unimaginable horrors, from imprisonment to debilitating illnesses, in addition to day-to-day frustrations that were no different from ours. They dealt with the same rivalries, political headwinds, drama, resistance, conservatism, breakups, stresses, and economic calamities. Or worse. Subjected to those pressures, these individuals were transformed for the better.

The book shares with you their collective wisdom in order to help you accomplish the very specific and increasingly urgent goal we all share: overcoming obstacles. Mental obstacles. Physical obstacles. Emotional obstacles. Perceived obstacles.

Before we get to the core lessons of the book, it is worth exploring the backstory of the book, which goes back to 2009 and a post on bestselling author Tim Ferriss’s popular blog. A guest post by Ryan on Stoicism prompted a publisher to instantly make their pitch: What about turning this into a book? Yet when Ryan asked his mentor, the bestselling author of 48 Laws of Power, Robert Greene, if he should take the deal, Robert said no. He thought it was too early and that Ryan needed to put my time into writing first.

“Against almost every instinct, I listened. I passed. The intervening years are a blur of events—some good and some pretty bad. I would rise pretty rapidly in business. Around that time, I became the Director of Marketing at American Apparel. The chaos and the conflict in that company—to say nothing of the temptations and responsibilities—would shape me as a person. I learned how to manage people, I learned how to maneuver and accomplish things. Mostly, I learned how to survive—crisis after crisis after crisis. The stuff that Ben Horowitz calls the hard things…”

All the difficulty and hardship would also be shaping his understanding of the material he would ultimately write about. Again, as Marcus would say, “the impediment to action advances action. What stands in the way becomes the way.”

What Marcus meant was that the Stoic finds a way to turn every negative into a positive. In this famous line, what he’s suggesting is that—no matter how bad or seemingly undesirable a situation becomes—we always have the opportunity to practice virtue, to use the situation as an opportunity to be our best selves. We don’t control when things get hard, but we always control how we respond. We can show patience, courage, humility, resourcefulness, reason, justice, and creativity. The things that test us make us who we are.

The Stoic grows stronger and better with every obstacle they face. They rally to every challenge and thrive as a result. So can you.

And that is in essence the core message of The Obstacle Is The Way, and the book illustrates with stories from the history’s greatest men and women—from Amelia Earhart to Steve Jobs to Teddy Roosevelt—this timeless principle. It shows a framework that we can use today—no matter what trying situation we find ourselves.

As the Haitian proverb puts it: Behind mountains are more mountains. One does not overcome one obstacle only to enter the land of no obstacles. No matter how successful we are or will be, we’re going to find things that stand in our path, and The Obstacle Is The Way shows us how to overcome them.

Three Key Takeaway Lessons from The Obstacle Is the Way

Overcoming obstacles is a discipline of three critical steps, and this is how the book is structured.

It begins with how we look at our specific problems, our attitude or approach; then the energy and creativity with which we actively break them down and turn them into opportunities; finally, the cultivation and maintenance of an inner will that allows us to handle defeat and difficulty.

It’s three interdependent, interconnected, and fluidly contingent disciplines: Perception, Action, and the Will.

The Discipline of Perception

Perception is how we see and understand what occurs around us—and what we decide those events will mean. Our perceptions can be a source of strength or of great weakness. If we are emotional, subjective and shortsighted, we only add to our troubles. To prevent becoming overwhelmed by the world around us, we must, as the ancients practiced, learn how to limit our passions and their control over our lives. It takes skill and discipline to bat away the pests of bad perceptions, to separate reliable signals from deceptive ones, to filter out prejudice, expectation, and fear. But it’s worth it, for what’s left is truth. While others are excited or afraid, we will remain calm and imperturbable. We will see things simply and straightforwardly, as they truly are—neither good nor bad. This will be an incredible advantage for us in the fight against obstacles.

The section opens with the story of John D. Rockefeller, and how he learned to steady himself and see things with ruthless objectivity during the Panic of 1857, and the lessons from it would shape him as an investor throughout his life. A key chapter in this section concerns itself with the key insight from the Samurai swordsman Miyamoto Musashi about the ‘perceiving eye’ which always sees “insurmountable obstacles” and “major setbacks.” Instead, we need to learn how to only see with our observing eye: only seeing what is there and not adding our own interpretations.

Perhaps the most important chapter in the first section of the book tells the story of how during World War II, the Allies, and specifically General Dwight D. Eisenhower, learned to shift their perspective and see how the revolutionary German war strategy of blitzkrieg, which seemed undefeatable, carried within itself its own destruction. As Eisenhower would say to his timid generals at a conference in Verdun, demonstrating the importance of optimism, perspective and defiance in the face of an immovable obstacle, “The present situation is to be regarded as opportunity for us and not disaster. There will be only cheerful faces at this conference table.”

The chapter is aptly called “Finding the Opportunity” and opens with this quote from Seneca: “A good person dyes events with his own color…and turns whatever happens to his own benefit.”

At the end of this section, you’ve acquired proper perception—objective, rational, ambitious, clean. You are able to isolate the obstacle in your way and expose it for what it is. But what comes next is to act.

The Discipline of Action

The second part of the book deals with how to take action. First, remember: Action is commonplace, right action is not. As a discipline, it’s not any kind of action that will do, but directed action. Everything must be done in the service of the whole. Step by step, action by action, we can dismantle the obstacles in front of us. With persistence and flexibility, we can act in the best interest of our goals. Action requires courage, not brashness—creative application and not brute force. Our movements and decisions define us: We must be sure to act with deliberation, boldness, and persistence. Those are the attributes of right and effective action. Nothing else—not thinking or evasion or aid from others. Action is the solution and the cure to our predicaments.

The section opens with the story of Demosthenes, one of the greatest orators of history. But as a kid he was sickly and frail with a nearly debilitating speech impediment. He was the awkward kid everyone laughed at. But he did something about it. To conquer his speech impediment, he would fill his mouth with pebbles and practice speaking. He rehearsed full speeches into the wind or while running up steep inclines. He even locked himself underground in a dugout he’d built to study and educate himself. All this training would pay off and make him one of the greatest orators of Athens. As some academic once asked him what the three most important traits of speechmaking were, his reply says it all: “Action, Action, Action!”

The rest of the section tells inspiring stories such as Amelia Earhart, the great aviator and first woman to fly solo nonstop across the atlantic, which teaches you the importance of just starting. It also looks at the incredible tenacity and persistence of both Ulysses S. Grant and Thomas Edison, and how slow pressure, repeated from many different angles, slowly and surely churns the solution to the top of the pile. The section also studies “The Process” — the strategy pioneered by coach Nick Saban that elite athletes use to focus on the task at hand. It also contains a masterclass in pragmatism, as illustrated by the stories of Sam Zemurray, the former CEO of United Fruit, who early on in his career was in competition to United Fruit and outmaneuvered the much stronger and better positioned corporation as a tiny small upstart.

And if the book is a Trojan House for Stoicism, this section can be seen as a Trojan Horse for thinking strategically. You learn timeless strategy lessons from the likes of George Washington (never attack where it is obvious, he would tell his men), the great strategist Saul Alinsky, Gandhi, Jigoro Kano, the founder of Judo, as well as the the great British historian and author of Strategy, B.H. Liddell Hart, who writes that “the Great Captain will take even the most hazardous indirect approach—if necessary over mountains, deserts or swamps, with only a fraction of the forces, even cutting himself loose from his communications. Facing, in fact, every unfavorable condition rather than accept the risk of stalemate invited by direct approach.”

But of course, some obstacles are impossible to overcome, some paths impassable. This is where the discipline of the Will comes.

The Discipline of the Will

Will is our internal power, which can never be affected by the outside world. It is our final trump card. If action is what we do when we still have some agency over our situation, the will is what we depend on when agency has all but disappeared. Placed in some situation that seems unchangeable and undeniably negative, we can turn it into a learning experience, a humbling experience, a chance to provide comfort to others. That’s will power. But that needs to be cultivated. We must prepare for adversity and turmoil, we must learn the art of acquiescence and practice cheerfulness even in dark times. Too often people think that will is how bad we want something. In actuality, the will has a lot more to do with surrender than with strength. Try “God willing” over “the will to win” or “willing it into existence,” for even those attributes can be broken. True will is quiet humility, resilience, and flexibility; the other kind of will is weakness disguised by bluster and ambition. See which lasts longer under the hardest of obstacles.

Take Abraham Lincoln. Most people are unaware that he battled crippling depression his entire life. His life was one of enduring and transcending great difficulty. It would be his own experience with suffering which drove his compassion to allay it in others. He was patient because he knew that difficult things took time. Above all, he found purpose and relief in a cause bigger than himself and his personal struggles, as the nation called for a leader of magnanimity during the Civil War. As crafty as he was, Lincoln’s strength was his will: the way he was able to resign himself to an onerous task without giving in to hopelessness, the way he was able to rise above the din and see politics philosophically. “This too shall pass” was Lincoln’s favorite saying, one he once said was applicable in any and every situation one could encounter.

Lincoln was strong and decisive as a leader. But he also embodied the Stoic maxim: sustine et abstine. Bear and forbear. Acknowledge the pain but trod onward in your task.

The section also tells the story of Theodore Roosevelt, who was sickly and fragile as a boy but as he would say with determination to his dad, “I’ll make my body,” developing what the Stoics would call an Inner Citadel, that fortress inside of us that no external adversity can ever break down. At the gym his father built, he worked out every single day, preparing him for the uniquely challenging life he would lead.

Other lessons in the book are familiar to any student of Stoicism: preparing ourselves for any negativity that may come our way (premeditatio malorum), loving whatever happens to us (amor fati), meditating on our mortality (memento mori).

***

In mastering these three disciplines we have the tools to flip any obstacle upside down. Like Rockefeller, we can be cool under pressure, immune to insults and abuse. We learn how to see opportunity in the darkest of places. We are able to direct our actions with energy and persistence. Like Demosthenes, we can assume responsibility for ourselves—teaching ourselves, compensating for disadvantages, and pursuing our rightful calling and place in the world. And like Lincoln, we realize that life is a trial. It will not be easy, but we are prepared and can give it everything.

In short, we can:

See things for what they are.

Do what we can.

Endure and bear what we must.

12 Best Quotes from The Obstacle Is the Way

“Whatever we face, we have a choice: Will we be blocked by obstacles, or will we advance through and over them?”

“There is no good or bad without us, there is only perception. There is the event itself and the story we tell ourselves about what it means.”

“Focusing exclusively on what is in our power magnifies and enhances our power.”

“Our perceptions determine, to an incredibly large degree, what we are and are not capable of. In many ways, they determine reality itself. When we believe in the obstacle more than in the goal, which will inevitably triumph?”

“There is always a countermove, always an escape or a way through, so there is no reason to get worked up. No one said it would be easy and, of course, the stakes are high, but the path is there for those ready to take it.”

“All we need to do is those three little duties—to try hard, to be honest, and to help others and ourselves. That’s all that’s been asked of us. No more and no less.”

“We decide what we will make of each and every situation. We decide whether we’ll break or whether we’ll resist.”

“Failure shows us the way—by showing us what isn’t the way.”

“It’s supposed to be hard. Your first attempts aren’t going to work. It’s going to take a lot out of you—but energy is an asset we can always find more of. It’s a renewable resource. Stop looking for an epiphany, and start looking for weak points. Stop looking for angels, and start looking for angles.”

“True will is quiet humility, resilience, and flexibility; the other kind of will is weakness disguised by bluster and ambition. See which lasts longer under the hardest of obstacles.”

“Wherever we are, whatever we’re doing and wherever we are going, we owe it to ourselves, to our art, to the world to do it well. That’s our primary duty. And our obligation. When action is our priority, vanity falls away.”

“You’ll have far better luck toughening yourself up than you ever will trying to take the teeth out of a world that is—at best—indifferent to your existence.”

The Obstacle Is the Way in Popular Culture

After its release, The Obstacle Is the Way slowly made its way through the community of professional sports, after being read number of prominent athletes and head coaches including Joe Maddon of the Chicago Cubs, UT basketball coach Shaka Smart, tennis pro James McGee, NFL lineman Garrett Gilkey, Olympic gold medalist Chandra Crawford, and others. On the way to their 2014 Super Bowl victory, Michael Lombardi and Bill Belichick of the New England Patriots distributed copies of The Obstacle Is the Way to their staff and players. In the 2015 season, Seattle Seahawks GM John Schneider and Pete Carroll passed the book around the team’s locker room. (Special thanks to Sunday Night Football commentator Michele Tafoya who we’ve also interviewed for the site.) Arnold Schwarzenegger and LL Cool J have also supposedly read and recommended the book.

The Obstacle Is The Way Products from Daily Stoic

While Ryan has the title of the book tattooed on his arm, many of the book’s readers have been asking for other ways to keep the timeless lessons from the book front of mind each and every day. Here are two products that we have created (no needles involved) that aim to accomplish exactly this.

Praise for The Obstacle Is the Way

“The book on stoicism that’s taking the NFL by storm.” – Sports Illustrated

“Follow these precepts and you will revolutionize your life. Read this book!” — Steven Pressfield, author of The War of Art and Gates of Fire

“A book for the bedside of every future—and current—leader in the world.” — Robert Greene, author of The 48 Laws of Power and Mastery

“An absolute must-read.” — Jimmy Soni, author of Rome’s Last Citizen

“First came Marcus Aurelius, then Frederick the Great . . . and now there’s you. This surprising book shows you how to craft a life of wonder by embracing obstacles and challenges.” — Chris Guillebeau, author of The $100 Startup

“A very, very good book with lots of examples about people who had to overcome great obstacles to have success.” — Nick Saban, head football coach at the University of Alabama

The Obstacle Is The Way Talks by Ryan Holiday

If you prefer, you can watch below Ryan present the book himself at Voice and Exit:

You might also like his TED talk on Stoicism and The Obstacle Is The Way